Okkervil River self-released their first album, Stars Too Small to Use, which led them to the South by Southwest music festival. After recording their first album in a garage, they signed with Jagjaguwar. They continued by releasing four more albums, including the critically lauded concept album Black Sheep Boy.[1]

After a period of touring for Black Sheep Boy, Okkervil River followed up with The Stage Names. The album sold 10,000 in its opening week in the United States. The group released a free covers album, Golden Opportunities Mixtape from their live performances.[2]

Scott Brackett playing trumpet at the 2007 Fun Fun Fest in Austin, Texas

Okkervil River's founding members became friends at Kimball Union Academy in Meriden, New Hampshire, and after parting ways for college moved to Austin, Texas to live together and start a band. The band consisted of singer-songwriter Will Sheff, Zach Thomas on bass and mandolin, and Seth Warren on drums. Their first gig was at Steamboat in Austin on 11 January 1999.[6]

In 1998, the group self-released their first disc, Bedroom EP. Over the course of two weekends in the summer of 1999, they recorded a seven-song self-released album titled Stars Too Small to Use, with recording engineer Jeff Hoskins.

They met Jonathan Meiburg at a gig with his band Whu Gnu at the Waterloo Brewing Company on December 3, 1999. Meiburg subsequently joined the band on accordion and later on pianos and organs.

On the strength of Stars Too Small to Use, Okkervil River was admitted into the 2000 SXSW music festival. Their first major press was a SXSW feature article[7] in the Austin Chronicle on 3 March 2000.

Don't Fall in Love with Everyone You See and Down the River of Golden DreamsEdit

By the time of that year's SXSW festival, Okkervil River had received interest in their new record from the Bloomington, Indiana-based record label Jagjaguwar. The record was released on Jagjaguwar on January 22, 2002.

One year later the band traveled to San Francisco and reunited with Warren to record their third album at Tiny Telephone with engineer Scott Solter at the console. Jagjaguwar released Down the River of Golden Dreams on 2 September 2003.

In 2003, Pedini left the band to pursue his graphic design work, leaving Okkervil River without a drummer for that year's SXSW. They invited Travis Nelsen, fresh off a tour filling in on drums for sister labelmates Secretly Canadian's Swearing at Motorists, to perform with them. He soon became the band's full-time drummer. The next year, during a long bout of touring, the band added keyboardist and lap-steel player Howard Draper as a fifth member.

In August 2004, the band began recording with Beattie again, finally putting the finishing touches on their third full-length album, Black Sheep Boy in November. It was released on 5 April 2005. As a result of the album's critical success, Okkervil River followed up with an EP entitled Black Sheep Boy Appendix on 22 November 2005. This was the first recording with Draper, horn and keyboardist Scott Brackett, guitarist Brian Cassidy, and touring bassist Pat Pestorius, who eventually replaced Zach Thomas in the band. The band signed to Virgin/EMI in Europe and the label re-released Black Sheep Boy and its follow-up Black Sheep Boy Appendix as a double disc on 28 April 2006. Jagjaguwar eventually followed suit, releasing the Definitive Edition with extra songs and videos.[8]

The Stage Names, their fourth full-length studio album (produced again by Beattie), was released on 7 August 2007. The disc features the line-up that toured extensively on Black Sheep Boy and the Black Sheep Boy Appendix, with Cassidy replacing Draper who joined Shearwater. The album was met with critical acclaim[9] and debuted at number 62 on the Billboard 200 with 10,000 copies sold.[10]

Okkervil River released their fifth album The Stand Ins on 9 September 2008.[11] In its first week, the album charted at No. 42 with 11,000 copies sold, according to the Billboard 200.[12] On 12 December 2007, the band freely released a nine-song mixtape entitled Golden Opportunities Mixtape via their website.[13] These recordings, along with the upcoming appendix, are the first to feature contributions from new touring keyboardist, Justin Sherburn, who joined the band in November 2007.

In 2008 guitarist Brian Cassidy stepped down from the band as a full-time touring member and was temporarily replaced by Charles Bissell of The Wrens for their spring and summer tours.[14] Bissell was later replaced by Lauren Gurgiolo, singer and songwriter of the Austin, Texas band The Dialtones. After performing on the Late Show with David Letterman in early 2009, the "Pop Lie" single was released backed with the b-sides "Millionaire" and "Pop Lie (One Man Band Version)".

Away, the band's eighth album, was released on 9 September 2016. The album features a new backing band and sonic direction, including contributions from Marissa Nadler, Jonathan Meiburg and members of the classical group yMusic.[18] The content of the album is largely based on Will Sheff's life during the 2013-2015 period after the release of The Silver Gymnasium, during which many members of the band left and his grandfather died.

In The Rainbow Rain was released on April 27, 2018, and marks the ninth album for the band. Will Sheff produced the album while Shawn Everett (Perfume Genius, Alabama Shakes, The War on Drugs) assumed mixing responsibilities.
The writing process incorporated Sheff's songwriting craftsmanship with an interplay of his new bandmates, Benjamin Lazar Davis (bass), Will Graefe (guitar), Lip Talk (Sarah K. Pedinotti) (keys) and Cully Symington (percussion) – the same iteration of Okkervil River that joined Sheff on the Away tour.[19]

Sheff and the band started work on the new album shortly after the end of that tour – and the presidential election. “If December 2016 was good for anything, it was good for writing songs,” he says. Sheff took a different approach to the album, sometimes co-writing with his new band, and occasionally attending local Quaker meetings.

In 2001, Meiburg and Sheff founded a second band known as Shearwater. Originally an outlet for Meiburg songs and some Sheff songs that didn't fit the Okkervil mold, Shearwater has gradually evolved into a full-fledged band. The band's 2006 release, Palo Santo (sans Sheff's vocals, but including his musical input), has seen Meiburg receive great critical acclaim. The groups still share many fans, and, while on tour together in 2004, they released a limited edition split-CD entitled Sham Wedding/Hoax Funeral. In 2008, Meiburg left Okkervil River to focus exclusively on Shearwater.

On 20 April 2010, former 13th Floor Elevators singer-guitarist Roky Erickson released the album True Love Cast Out All Evil, produced by Will Sheff and backed by Okkervil River.